I haven't been writing much lately because I've been doing a lot of writing in other places, over at test IO and for Democrats Abroad. After spending the weekend moderating (and facilitating workshops that I designed) the annual general meeting of Democrats Abroad, I've been thinking a lot what it means to ask good questions.

Some questions are so insightful and present a special perspective on the issue. It's immediately clear that the question-asker has thought deeply and engaged with the subject. Sometimes questions are an attempt to seem smart in front of a group. Sometimes questions aren't even questions, but long-winded statements that end with "I'd like to know what you think about that."

Lately, I've been interviewing people inside companies in order to put together some case studies on how they're using a product. One of my predecessors put together a long list of questions that they would send to the contacts. Many of these were pretty banal, like "how many people are on your team?"

I don't think it's wrong to ask these questions. Sometimes you need to lay some groundwork before you can get to the really interesting topics. But my goal is to get a sense of the company on a high level and then go into more detail on the parts of their work process that I'm interested in, so a few easy questions to start off with help warm the interviewee up.

What I did notice though, is that a lot of the questions are too easy. It felt more like the checklist in a doctor's office (Where does it hurt? How long? What medications are you taking?) than an invitation to have a conversation and for the respondent to share. By asking questions that show you're engaging and thinking about what someone has told you, you're showing them that you're really listening and that you care about what they have to say.

Usually people talk about how we get in trouble if we are content with easy answers. In this case, it's the easy questions that we shouldn't settle for.